7-phenyl-9-oxa-6-azatricyclo[8.4.0.0^1,6]tetradec-4-en-10-ylamine | 855301-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 7-phenyl-9-oxa-6-azatricyclo[8.4.0.0^1,6]tetradec-4-en-10-ylamine
• 英文别名: (1S,7R,10S)-7-phenyl-9-oxa-6-azatricyclo[8.4.0.01,6]tetradec-4-en-10-amine
• CAS: 855301-95-0
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: JWVOOOFAIRPNBK-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-phenyl-9-oxa-6-azatricyclo[8.4.0.0^1,6]tetradec-4-en-10-ylamine 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 氢气 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 99.25h， 生成 1-[2-(tert-butoxydimethylsilanyloxy)-1-phenylethyl]-1-azaspiro[5.5]undecan-7-ol
  参考文献：
  名称：

  Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(R,S) Building Block

  摘要：

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.

  DOI：

  10.1021/jo050258d
• 作为产物：
  描述：

  5-(4-chlorobutyl)-3-phenylhexahydrooxazolo[3,2-a]pyridine-5-carbonitrile 在 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 7-phenyl-9-oxa-6-azatricyclo[8.4.0.0^1,6]tetradec-4-en-10-ylamine
  参考文献：
  名称：

  Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(R,S) Building Block

  摘要：

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.

  DOI：

  10.1021/jo050258d

文献信息

• Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(<i>R</i>,<i>S</i>) Building Block
  作者：Emmanuel Roulland、Fabrice Cecchin、Henri-Philippe Husson

  DOI：10.1021/jo050258d

  日期：2005.5.1

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.